Wonderful Winter Things To Do In Key West

If you thought Key West was only a summertime destination, think again! This unique island city has plenty to offer visitors all year-round — including in the winter. From cooler weather and fewer crowds to festive events and holiday traditions, there’s something for everyone in Key West during the colder months. Here are just a few of the many reasons why you should consider spending your winter vacation in this sunny Florida spot.

Key West Winters

A “winter wonderland” in Key West looks more like a beautiful beach paradise. With temperatures generally hovering in the mid-70s each day and hardly ever dropping below 65 degrees, it’s no wonder so many tourists choose to flock to our magnificent little island each year at this time! So, while most people elsewhere are dreaming of fireside evenings, snowshoeing and winter break skiing trips, Key West locals start planning barbecues in the park, fishing trips on the pier or simply sunning themselves on one of the local beaches.

Why Visit Key West in the Winter

Key West in winter is a real tropical paradise. While other people are stuck in the cold and snow, you can hide away from the chill on an island of sunshine. Splash around in turquoise waters and beach comb along your own private paradise. Experience endless days of sunny skies by exploring by foot or taking a trolley tour to get a glimpse of the Key West culture. From succulent seafood restaurants to historic monuments, visiting Key West in winter means you’ll get all the blissful beauty without the scorching summer heat!

Places to Visit

Truman Little White House Events Calendar

With winter quickly approaching, don’t let cabin fever set in! Instead, head south to the Truman Little White House and add a bit of tropical flavor to the cold winter months. From historical tours to special museum events, there’s something for everyone at this wintry Key West getaway. From learning about Harry S. Truman and the unique history of this historic building to simply enjoying the climate change from winter snow to sunny island days, don’t hibernate this winter. Explore the variety of events and activities at the Truman Little White House. Plan your visit to the Truman Little White House and escape the rainy or winter weather by immersing yourself in the rich history and warm atmosphere of this Key West gem.

Sails to Rails Museum

Embark on a journey through Key West’s maritime past at the captivating Sails to Rails Museum. Discover the transition from sailboats to steamships and railways that shaped the island’s history. Explore artifacts, lift a real silver bar, and delve into maritime tales. Immerse yourself in Key West’s heritage with a Fort Jefferson diorama, offering a glimpse into its strategic importance.

Explore Iconic Duval Street

Duval Street is one of the most iconic streets in Florida, a winter oasis in a tropical climate. Barhopping, perusing boutique shops, finding an amazing seafood meal or taking in some of the local attractions are all great options on Duval Street — even if winter temperatures sometimes arrive with a chill. The street is lively, vibrant and full of surprises. Get ready to experience some of the wildest outdoor music scenes that South Florida has to offer!

Stop by the Southernmost Point of the Continental U.S.

On a lively island such as Key West, nothing will warm your winter better than the fabulous nightlife, delicious seafood and orange sunsets, not to mention the biggest attraction — taking a selfie at the Southernmost Point. Who wouldn’t want bragging rights for getting there faster than anyone else in winter?

Key West Aquarium

Step right up to the Key West Aquarium and see some of the rarest winter critters around! Tour its tropical wonders and observe fascinating species, such as the moon jellyfish or barracuda, not to mention delightful residents such as sea turtles, sharks, tropical fish and more. It’s an enchanting place that is sure to make winter slip by in no time!

Key West Lighted Boat Parade

Every winter in Key West, boats appear to come alive in a spectacular event known as the Key West Lighted Boat Parade. Boats of all shapes and sizes shimmer and twinkle with brilliant displays of colorful lights while they cruise along Key West Harbor. With many festive decorations and spirited music, this annual winter tradition is something that makes anyone who views it feel merry and bright!

Enjoy the Music Festival Mile 0 Fest

Located in sunny Key West, this wintertime music festival offers a chance to escape from the cold and dive into some really hot jams. Check out sets from local and international artists, then end your night dancing under the stars with a drink in one hand and someone special by your side. Whatever kind of winter blues you have, this festival has got just what is needed to heat things up.

Take a Sunset Cruise

Winter sunsets can be particularly stunning sights — and what better way to experience one than by taking a sunset cruise? Head down to Key West for a pristine view of the winter sun sinking from day into night, the golden light dancing across the sky and the glittering waters ahead. Feel the winter sun on your skin as you breathe in the fresh sea air with a wineglass in hand. Whether it’s a romantic evening or an evening spent with friends, there’s no better place to be than out at sea watching winter end its day.

Visit the Key West Butterfly and Nature Conservatory

Make winter a little more bearable and head to Key West Butterfly and Nature Conservatory. Stop off on the sunny island of Key West and get lost in this mesmerizing aviary full of exotic butterflies and birds. Take a tour of the conservatory with experts who can share fun facts about the creatures around you and explain the various elements that make it possible for them to flourish. Enjoy the winter day with kaleidoscopic colors and patterns that will have you convinced you are walking through an enchanted garden.


From exploring Duval Street to stopping by the Southernmost Point of the continental U.S., there are plenty of iconic landmarks to check off your bucket list. And, don’t forget about enjoying live music at one of the many festivals or taking a sunset cruise — two perfect ways to end any day in paradise. Key West is the winter getaway with something for everyone in the family.


What are the best activities for families in Key West in the winter?

Winter in Key West may be the best season of all to visit! Not only is the weather perfect for escaping the icy Northeast, but there are also plenty of fun-filled family activities that just can’t be beaten. From kayaking or canoeing through crystal-blue waters to visiting the famous Ernest Hemingway Home and Museum, nature lovers of all ages will find something new and exciting. For a unique experience, families can finally crack open those old fiction novels they never read back in school with a book tour around town. Finally, get your cameras ready for incredible sunsets at Mallory Square — the perfect way to end each day!

What are the best beaches in Key West in the winter?

Winter in Key West is the best time to visit if you want to beat the crowds and find some truly magical beaches. Smathers Beach offers a stunning half-mile expanse of bright white sand, making it the perfect spot for a romantic sunset stroll. And, Higgs Beach is like something out of a fantasy novel, with turquoise waters, lush palm trees and plenty of spots for swimming and kayaking. The historic White Street Pier offers another great beach option for spotting some exciting marine life.

Is it still warm enough to go to the beach in the winter?

Visiting the beach in the winter can be a unique experience, especially in Key West! It’s still warm enough down here to enjoy nearly any outdoor activity outside of the water. Strolling along the sand and soaking up the sunshine is always a fantastic way to spend an afternoon.

What are some of the best winter festivals in Key West?

During the winter season in Key West, Florida, visitors can experience a range of vibrant and entertaining festivals that showcase the island’s rich culture and warm hospitality. One of the most anticipated events is the Key West Holiday Fest, which typically takes place throughout December, featuring a parade of illuminated boats, holiday concerts, and a tree lighting ceremony at the Historic Harbor Walk. Another must-attend event is the Annual Key West Food and Wine Festival, held in late January, which boasts a vast array of gourmet food, exceptional wines, and exquisite culinary events hosted by renowned chefs, winemakers, and sommeliers. Additionally, the Key West Literary Seminar held in January welcomes both acclaimed authors and literature enthusiasts to engage in discussions, lectures, and workshops on various literary themes, thus providing an excellent opportunity for intellectual enrichment with the picturesque backdrop of the island.

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